NP-MRD: Showing NP-Card for 5,8-diepi-ilimaquinone (NP0043479)

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Record Information

Version

1.0

Created at

2021-06-21 00:52:45 UTC

Updated at

2021-06-30 00:19:10 UTC

NP-MRD ID

NP0043479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,8-diepi-ilimaquinone

Provided By

JEOL Database JEOL Logo

Description

5-Epiilimaquinone belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. 5,8-diepi-ilimaquinone is found in Dactylospongia elegans, Hippospongia sp., Petrosaspongia metachromia and Polyfibrospongia australis. It was first documented in 2000 (PMID: 10785412). Based on a literature review very few articles have been published on 5-Epiilimaquinone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102523D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102523D          

 56 58  0  0  0  0            999 V2000
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   -1.5838   -3.0623   -2.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1916   -1.0807   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -3.5958   -3.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891   -3.3870   -2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775   -4.6579   -2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -2.8617   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505   -3.7865   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180   -1.7189    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.9134    1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    0.4045    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    0.7489    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.7355    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189   -0.7878   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5627    0.8027   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -0.7690   -1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    0.6444   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.2036   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    1.6519   -2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    3.4714    0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875    5.7397    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1153    4.3537   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0013    2.9798   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074    3.9471   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  0  0  0  0
  3  2  1  0  0  0  0
  6 13  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 16 25  1  0  0  0  0
 17 19  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 25  1  0  0  0  0
 10 11  1  0  0  0  0
 25 26  2  0  0  0  0
 13 11  1  0  0  0  0
 19 20  2  0  0  0  0
  2  7  1  0  0  0  0
 22 23  1  0  0  0  0
  6  5  1  0  0  0  0
 23 24  1  0  0  0  0
  6  7  1  0  0  0  0
  2  1  2  3  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 11 12  1  0  0  0  0
 18 17  1  0  0  0  0
  6 35  1  1  0  0  0
 16 15  1  0  0  0  0
  7  8  1  6  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  5 33  1  0  0  0  0
  5 34  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
 10 41  1  0  0  0  0
 10 42  1  0  0  0  0
 11 43  1  1  0  0  0
 18 52  1  0  0  0  0
 15 50  1  0  0  0  0
 15 51  1  0  0  0  0
 21 53  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
 14 49  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
 12 46  1  0  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)C(OC([H])([H])[H])=C([H])C1=O)C([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C(=C([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18-,21+,22-/m1/s1

> <INCHI_KEY>
JJWITJNSXCXULM-FPNURHQBSA-N

> <FORMULA>
C22H30O4

> <MOLECULAR_WEIGHT>
358.478

> <EXACT_MASS>
358.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.60874912905912

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-{[(1R,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
4.367249087666668

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.868666424764576

> <JCHEM_PKA_STRONGEST_BASIC>
-4.944412504654549

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
104.14519999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1R,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
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    2.0943    2.8274   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4520    4.4877    0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271    5.0557    1.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394    4.9373    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8528    4.3921   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1464    4.8933   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1802    3.9797   -0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    3.3374   -1.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129    3.0798   -2.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458   -3.8753   -2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471   -3.7823   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8955   -3.5723   -4.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738   -3.0898   -4.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.3969   -5.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5775   -4.6579   -2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7505   -3.7865   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0305    0.4045    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    0.7489    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.7355    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189   -0.7878   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5627    0.8027   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -0.7690   -1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    0.6444   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.2036   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    1.6519   -2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    3.4714    0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875    5.7397    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1153    4.3537   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0013    2.9798   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074    3.9471   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0
  4  3  1  0
  4  5  1  0
  3  2  1  0
  6 13  1  0
  7  9  1  0
  9 10  1  0
 16 25  1  0
 17 19  1  0
 19 21  1  0
 21 22  2  0
 22 25  1  0
 10 11  1  0
 25 26  2  0
 13 11  1  0
 19 20  2  0
  2  7  1  0
 22 23  1  0
  6  5  1  0
 23 24  1  0
  6  7  1  0
  2  1  2  3
 13 14  1  6
 13 15  1  0
 11 12  1  0
 18 17  1  0
  6 35  1  1
 16 15  1  0
  7  8  1  6
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  5 33  1  0
  5 34  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 18 52  1  0
 15 50  1  0
 15 51  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
  1 27  1  0
  1 28  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.672  -3.597  -2.193  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.584  -3.062  -2.776  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.589  -2.863  -4.278  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.211  -1.443  -4.668  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.066  -0.959  -3.986  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.120  -1.159  -2.444  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.286  -2.641  -2.053  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.828  -3.623  -2.530  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.321  -2.815  -0.507  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.050  -1.709   0.242  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.440  -0.328  -0.053  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.982  -0.276   0.531  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.552   0.018  -1.584  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.054   0.177  -1.919  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.176   1.390  -1.932  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.124   2.644  -1.121  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.785   3.270  -0.354  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.094   2.827  -0.253  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.452   4.488   0.429  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.327   5.056   1.074  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.939   4.937   0.441  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.853   4.392  -0.366  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.146   4.893  -0.312  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.180   3.980  -0.669  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.429   3.337  -1.347  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.113   3.080  -2.332  0.00  0.00           O+0
HETATM   27  H   UNK     0      -3.546  -3.875  -2.777  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.747  -3.782  -1.128  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.896  -3.572  -4.743  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.574  -3.090  -4.707  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.072  -1.397  -5.755  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.046  -0.771  -4.452  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.247   0.081  -4.267  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.907  -1.508  -4.429  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.192  -1.081  -2.207  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.997  -3.596  -3.610  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.789  -3.387  -2.058  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.578  -4.658  -2.266  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.707  -2.862  -0.124  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.751  -3.787  -0.231  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.118  -1.719   0.007  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.991  -1.913   1.319  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.030   0.405   0.515  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.316   0.749   0.668  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.012  -0.736   1.525  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.719  -0.788  -0.093  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.563   0.803  -1.179  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.595  -0.769  -1.931  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.201   0.644  -2.896  0.00  0.00           H+0
HETATM   50  H   UNK     0       1.258   1.204  -1.912  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.034   1.652  -2.976  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.544   3.471   0.337  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.188   5.740   1.124  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.115   4.354  -0.240  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.001   2.980  -0.259  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.307   3.947  -1.754  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    3    7    1                                                  
CONECT    3    4    2   29   30                                             
CONECT    4    3    5   31   32                                             
CONECT    5    4    6   33   34                                             
CONECT    6   13    5    7   35                                             
CONECT    7    9    2    6    8                                             
CONECT    8    7   36   37   38                                             
CONECT    9    7   10   39   40                                             
CONECT   10    9   11   41   42                                             
CONECT   11   10   13   12   43                                             
CONECT   12   11   44   45   46                                             
CONECT   13    6   11   14   15                                             
CONECT   14   13   47   48   49                                             
CONECT   15   13   16   50   51                                             
CONECT   16   17   25   15                                                  
CONECT   17   16   19   18                                                  
CONECT   18   17   52                                                       
CONECT   19   17   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   22   53                                                  
CONECT   22   21   25   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   54   55   56                                             
CONECT   25   16   22   26                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    5                                                            
CONECT   35    6                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   10                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   12                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   15                                                            
CONECT   51   15                                                            
CONECT   52   18                                                            
CONECT   53   21                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
   -2.6724   -3.5973   -2.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838   -3.0623   -2.7760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5895   -2.8630   -4.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2111   -1.4427   -4.6677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0655   -0.9587   -3.9857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -1.1594   -2.4439 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2864   -2.6413   -2.0527 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8276   -3.6228   -2.5299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3213   -2.8154   -0.5075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0496   -1.7086    0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4404   -0.3281   -0.0530 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9816   -0.2763    0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5519    0.0179   -1.5844 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0541    0.1765   -1.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    1.3903   -1.9316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1236    2.6437   -1.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7845    3.2698   -0.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0943    2.8274   -0.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4520    4.4877    0.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271    5.0557    1.0738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9394    4.9373    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8528    4.3921   -0.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1464    4.8933   -0.3119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1802    3.9797   -0.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    3.3374   -1.3468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1129    3.0798   -2.3319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5458   -3.8753   -2.7766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7471   -3.7823   -1.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8955   -3.5723   -4.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5738   -3.0898   -4.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.3969   -5.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0455   -0.7709   -4.4519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    0.0812   -4.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9065   -1.5083   -4.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1916   -1.0807   -2.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9972   -3.5958   -3.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891   -3.3870   -2.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5775   -4.6579   -2.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066   -2.8617   -0.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505   -3.7865   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1180   -1.7189    0.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9906   -1.9134    1.3190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0305    0.4045    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158    0.7489    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.7355    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7189   -0.7878   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5627    0.8027   -1.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5950   -0.7690   -1.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2009    0.6444   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2579    1.2036   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0339    1.6519   -2.9758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5438    3.4714    0.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875    5.7397    1.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1153    4.3537   -0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0013    2.9798   -0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3074    3.9471   -1.7540 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  2  0
  4  3  1  0
  4  5  1  0
  3  2  1  0
  6 13  1  0
  7  9  1  0
  9 10  1  0
 16 25  1  0
 17 19  1  0
 19 21  1  0
 21 22  2  0
 22 25  1  0
 10 11  1  0
 25 26  2  0
 13 11  1  0
 19 20  2  0
  2  7  1  0
 22 23  1  0
  6  5  1  0
 23 24  1  0
  6  7  1  0
  2  1  2  3
 13 14  1  6
 13 15  1  0
 11 12  1  0
 18 17  1  0
  6 35  1  1
 16 15  1  0
  7  8  1  6
  4 31  1  0
  4 32  1  0
  3 29  1  0
  3 30  1  0
  5 33  1  0
  5 34  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  1
 18 52  1  0
 15 50  1  0
 15 51  1  0
 21 53  1  0
 24 54  1  0
 24 55  1  0
 24 56  1  0
  1 27  1  0
  1 28  1  0
 14 47  1  0
 14 48  1  0
 14 49  1  0
 12 44  1  0
 12 45  1  0
 12 46  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₃₀O₄

Average Mass

358.4780 Da

Monoisotopic Mass

358.21441 Da

IUPAC Name

3-{[(1R,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

Traditional Name

3-{[(1R,2R,4aR,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C(C(=O)C(OC([H])([H])[H])=C([H])C1=O)C([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C(=C([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18-,21+,22-/m1/s1

InChI Key

JJWITJNSXCXULM-FPNURHQBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dactylospongia elegans	JEOL database	Du, L., et al, J. Nat. Prod. 76, 1175 (2013)
Hippospongia sp.	-	KNApSAcK
Petrosaspongia metachromia	-	KNApSAcK
Polyfibrospongia australis	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
Quinone
P-benzoquinone
Vinylogous ester
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.89	ALOGPS
logP	4.37	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	5.87	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.15 m³·mol⁻¹	ChemAxon
Polarizability	39.61 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30770979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71726091

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Salmoun M, Devijver C, Daloze D, Braekman JC, Gomez R, de Kluijver M, Van Soest RW: New sesquiterpene/quinones from two sponges of the genus Hyrtios. J Nat Prod. 2000 Apr;63(4):452-6. doi: 10.1021/np9903346. [PubMed:10785412 ]
Du, L., et al. (2013). Du, L., et al, J. Nat. Prod. 76, 1175 (2013). J. Nat. Prod..

Showing NP-Card for 5,8-diepi-ilimaquinone (NP0043479)

MOL for NP0043479 (5,8-diepi-ilimaquinone)

3D MOL for NP0043479 (5,8-diepi-ilimaquinone)

3D SDF for NP0043479 (5,8-diepi-ilimaquinone)

3D-SDF for NP0043479 (5,8-diepi-ilimaquinone)

PDB for NP0043479 (5,8-diepi-ilimaquinone)

3D PDB for NP0043479 (5,8-diepi-ilimaquinone)

SMILES for NP0043479 (5,8-diepi-ilimaquinone)

INCHI for NP0043479 (5,8-diepi-ilimaquinone)

Structure for NP0043479 (5,8-diepi-ilimaquinone)

3D Structure for NP0043479 (5,8-diepi-ilimaquinone)